Acetic Acid → HCID 10336229, compound

HRID 731522Notes

Reaction equation

HRID 731522 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[C:12]1(=O)[CH2:15][CH2:14][CH2:13]1.[C:17](O)(=O)[CH3:18].[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:22].[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH:18]2[CH2:17][CH2:22][CH2:21]2)[CH:12]2[CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 12376816HCID 12376816, compound

Product 1

HCID 10336229HCID 10336229, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3-(4-Bromophenyl)propan-1-amine (0.50 g, 2.34 mmol; described in: Davies, R. V. et al. J. Chem. Soc. Perkin Trans. 1 1977, 2357-2364), cyclobutanone (0.393 g, 5.61 mmol) and acetic acid (0.140 mL, 2.34 mmol) were mixed in dichloroethane (6 mL) and stirred for 30 min. Sodium triacetoxy borohydride was added and the reaction mixture was stirred for 15 h. The reaction was quenched with water (15 mL) and extracted with methylene chloride (50 mL). The organic phase was separated, dried and evaporated. Purification by column chromatography using methylene chloride to methylene chloride/methanol, (2:1), gradient as the eluent gave 0.32 g (42% yield) of the title compound as colorless oil: MS (ESI) m/z 322 and 324 (M++1).

Workup

  1. stirringthe reaction mixture was stirred for 15 h
  2. customThe reaction was quenched with water (15 mL)
  3. extractionextracted with methylene chloride (50 mL)
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-ad4d36050f1d4242a5127972bfed6f7d
Source dataset
uspto-grants-2009_09
Patent number
US07585853B2

Reaction notes

Loading…